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Literature DB >> 20441180

Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.

Abstract

A methoxypyridine serves as a masked pyridone in a concise synthesis of the Lycopodium alkaloid lycoposerramine R, which has been prepared for the first time. The key step of the synthesis is the use of an Eschenmoser Claisen rearrangement to forge a key quaternary carbon center.

Entities: Chemical Disease

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Year: 2010 PMID： 20441180 PMCID： PMC2878394 DOI： 10.1021/ol100823t

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

9 in total

Review 1. Claisen rearrangement over the past nine decades.

Authors: Ana M Martín Castro
Journal: Chem Rev Date: 2004-06 Impact factor: 60.622

2. Gold(I)-catalyzed cyclizations of silyl enol ethers: application to the synthesis of (+)-lycopladine A.

Authors: Steven T Staben; Joshua J Kennedy-Smith; David Huang; Britton K Corkey; Rebecca L Lalonde; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2006-09-11 Impact factor: 15.336

3. Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.

Authors: Kimberly K Larson; Richmond Sarpong
Journal: J Am Chem Soc Date: 2009-09-23 Impact factor: 15.419

Review 4. The Lycopodium alkaloids.

Authors: Xiaoqiang Ma; David R Gang
Journal: Nat Prod Rep Date: 2004-10-21 Impact factor: 13.423

5. Concise total synthesis of (+/-)-lycopladine A.

Authors: John E DeLorbe; Monica D Lotz; Stephen F Martin
Journal: Org Lett Date: 2010-04-02 Impact factor: 6.005

6. Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation.

Authors: Scott P West; Alakesh Bisai; Andrew D Lim; Raja R Narayan; Richmond Sarpong
Journal: J Am Chem Soc Date: 2009-08-12 Impact factor: 15.419

7. A general bifunctional catalyst for the anti-Markovnikov hydration of terminal alkynes to aldehydes gives enzyme-like rate and selectivity enhancements.

Authors: Douglas B Grotjahn; Daniel A Lev
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

8. A convergent approach to huperzine A and analogues.

Authors: Seán A Kelly; Yann Foricher; John Mann; Jonathan M Bentley
Journal: Org Biomol Chem Date: 2003-08-21 Impact factor: 3.876

9. Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.

Authors: Alakesh Bisai; Scott P West; Richmond Sarpong
Journal: J Am Chem Soc Date: 2008-05-14 Impact factor: 15.419

9 in total

6 in total

1. Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors: Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal: J Org Chem Date: 2012-12-28 Impact factor: 4.354

Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.

Review 1. Claisen rearrangement over the past nine decades.

2. Gold(I)-catalyzed cyclizations of silyl enol ethers: application to the synthesis of (+)-lycopladine A.

3. Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.

Review 4. The Lycopodium alkaloids.

5. Concise total synthesis of (+/-)-lycopladine A.

6. Total synthesis of (+)-lyconadin A and related compounds via oxidative C-N bond formation.

7. A general bifunctional catalyst for the anti-Markovnikov hydration of terminal alkynes to aldehydes gives enzyme-like rate and selectivity enhancements.

8. A convergent approach to huperzine A and analogues.

9. Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.

1. Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

2. Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.

3. Synthesis of the pentacyclic skeleton of the indole alkaloid arboflorine.

4. Synthetic studies toward the citrinadin A and B core architecture.

5. Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging.

6. Lyconadins G and H, Two Rare Lyconadin-Type Lycopodium Alkaloids from Lycopodium complanatum.